In December 1861, Tipton County Court Clerk John T. Douglas feared that the coming year might bring the bloodiest war America had ever known. On June 10, 1861, 943 residents of Tipton County voted for secession and only 16 voted against it, while local men had already begun forming volunteer military companies. The first, the Tipton Rifles, trained at the old fairgrounds in Covington under Capt. John Turner before leaving for Germantown to join the 4th Tennessee Infantry, and the county ultimately furnished twelve companies to the Confederacy. Although West Tennessee quickly fell under Union control, Confederate Col. Robert V. Richardson completed the organization of the 1st Tennessee Regiment of Partisan Rangers at its main camp near Bloomington, and Federal efforts to curb the Rangers led to numerous engagements across the county. The largest took place in the Lemmon Woods near Covington in March 1863, where Union Col. Benjamin H. Grierson’s cavalry attacked and scattered the Confederates and then destroyed their camp and equipment. Most of Tipton County escaped direct damage from the war except Randolph, where in September 1862 guerillas fired on an unarmed Union packet boat carrying relief goods for Southern families, prompting Union Gen. William T. Sherman to order the town destroyed with one house left standing to mark its location. Two years later, Confederate partisans tried to seize the steamer Belle Saint Louis at the Randolph landing but were driven off after a short fight.